Sodium Hydroxide → HCID 56591603, compound

HRID 2047698Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:16]=1)[CH2:9][C:8]2([CH3:28])[CH3:27])=[O:4].[OH-].[Na+]>O1CCCC1.CO.O>[CH3:27][C:8]1([CH3:28])[C:7]2[C:12](=[CH:13][CH:14]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)[NH:11][CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:16]=2)[CH2:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (100 mg, 0.3 mmol) in tetrahydrofuran (2 mL) and methanol (2 mL) was added 3 N sodium hydroxide (1 mL). The reaction mixture was stirred at 80° C. for 6 hours, and then diluted with water (10 mL), extracted with diethyl ether (20 mL). The organic layer was discarded. The aqueous layer was acidified with concentrated hydrochloric acid to pH 4 and extracted with ethyl acetate (40 mL×3); and the combined organics were dried over anhydrous Na2SO4 The solvent was removed in vacuo and purified by preparative HPLC to afford 4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (50 mg, 52%) as a yellow foam. MS (ESI+) [(M+H)+] 367.2.

Workup

extractionextracted with diethyl ether (20 mL)
extractionextracted with ethyl acetate (40 mL×3)
dry with materialand the combined organics were dried over anhydrous Na2SO4 The solvent
customwas removed in vacuo
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-93050e4633be4e6d94d25c97149e8e64
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592594B2

Reaction notes

Loading…